engagement and rings

my so of 3 years has been on and off talking about rings and engagement. I showed him a few under $500 rings but he says I need a more expensive one but we dont have that kind of money. he's not the guy at all to do surprises or anything special either. should I mention it again? I have a promise ring that he gave me 2 years ago but it was a $10 ring from Wal-Mart so its all woren out and pink from the silver rubbing off...